The DOI matches its Crossref record; 80 of the 80 references it cites were found in a registry or an index.
Interaction of Estrogenic Chemicals and Phytoestrogens with Estrogen Receptor β
Abstract
The rat, mouse and human estrogen receptor (ER) exists as two subtypes, ER alpha and ER beta, which differ in the C-terminal ligand-binding domain and in the N-terminal transactivation domain. In this study, we investigated the estrogenic activity of environmental chemicals and phytoestrogens in competition binding assays with ER alpha or ER beta protein, and in a transient gene expression assay using cells in which an acute estrogenic response is created by cotransfecting cultures with recombinant human ER alpha or ER beta complementary DNA (cDNA) in the presence of an estrogen-dependent reporter plasmid. Saturation ligand-binding analysis of human ER alpha and ER beta protein revealed a single binding component for [3H]-17beta-estradiol (E2) with high affinity [dissociation constant (Kd) = 0.05 - 0.1 nM]. All environmental estrogenic chemicals [polychlorinated hydroxybiphenyls, dichlorodiphenyltrichloroethane (DDT) and derivatives, alkylphenols, bisphenol A, methoxychlor and chlordecone] compete with E2 for binding to both ER subtypes with a similar preference and degree. In most instances the relative binding affinities (RBA) are at least 1000-fold lower than that of E2. Some phytoestrogens such as coumestrol, genistein, apigenin, naringenin, and kaempferol compete stronger with E2 for binding to ER beta than to ER alpha. Estrogenic chemicals, as for instance nonylphenol, bisphenol A, o, p'-DDT and 2',4',6'-trichloro-4-biphenylol stimulate the transcriptional activity of ER alpha and ER beta at concentrations of 100-1000 nM. Phytoestrogens, including genistein, coumestrol and zearalenone stimulate the transcriptional activity of both ER subtypes at concentrations of 1-10 nM. The ranking of the estrogenic potency of phytoestrogens for both ER subtypes in the transactivation assay is different; that is, E2 >> zearalenone = coumestrol > genistein > daidzein > apigenin = phloretin > biochanin A = kaempferol = naringenin > formononetin = ipriflavone = quercetin = chrysin for ER alpha and E2 >> genistein = coumestrol > zearalenone > daidzein > biochanin A = apigenin = kaempferol = naringenin > phloretin = quercetin = ipriflavone = formononetin = chrysin for ER beta. Antiestrogenic activity of the phytoestrogens could not be detected, except for zearalenone which is a full agonist for ER alpha and a mixed agonist-antagonist for ER beta. In summary, while the estrogenic potency of industrial-derived estrogenic chemicals is very limited, the estrogenic potency of phytoestrogens is significant, especially for ER beta, and they may trigger many of the biological responses that are evoked by the physiological estrogens.
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In the citing paper
“BPA has steroid-like properties and binds to both estrogen receptors (ERα, ERβ) with low affinity [22], [23].”
From Gestational Exposure to Low Dose Bisphenol A Alters Social Behavior in Juvenile Mice (2011) · cites this paper as [22]
In the citing paper
“which is one of the most potent EDCs on nuclear estrogen receptors (ERs), particularly ERβ (82, 83).”
From Endocrine Disruption of Vasopressin Systems and Related Behaviors (2017) · cites this paper as [82]
In the citing paper
“Given the comparatively higher promiscuity of ERβ (relative to ERα) for ligands including multiple phytoestrogens including GEN (82), and even the androgen metabolite 5α-androstane-3β,17β-diol (3β-diol) (141), this is a strikingly understudied but likely avenue for endocrine disruption.”
From Endocrine Disruption of Vasopressin Systems and Related Behaviors (2017) · cites this paper as [82]
In the citing paper
“Genistein is structurally similar to oestrogen and may influence breast cancer risk through oestrogen receptor binding, which has been demonstrated in vitro [135,136].”
From Fermented foods: definitions and characteristics, impact on the gut microbiota and effects on gastrointestinal health and disease (2019) · cites this paper as [136]
In the citing paper
“Genistein is structurally similar to oestrogen and may influence breast cancer risk through oestrogen receptor binding, which has been demonstrated in vitro [135,136].”
From Fermented foods: definitions and characteristics, impact on the gut microbiota and effects on gastrointestinal health and disease (2019) · cites this paper as [136]
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Metadata
- Authors
- Kuiper, G. G. J. M., Lemmen, J. G., Carlsson, B., Corton, J. C., Safe, S. H., van der Saag, P. T., van der Burg, B., & Gustafsson, J.-Å.
- Affiliations
- Karolinska Institutet (SE)
- Hubrecht Institute for Developmental Biology and Stem Cell Research (NL)
- Texas A&M University (US)
- Venue
- Endocrinology
- Publisher
- The Endocrine Society
- Published
- 1998-10
- Volume
- 139
- Issue
- 10
- Pages
- 4252-4263
- ISSN
- 0013-7227 (ISSN-L)
- 1945-7170
- OpenAlex
- W2049970571
- Cited by
- 4,203
- References
- 80
- Citations by year
- 2026: 44 · 2025: 77 · 2024: 73 · 2023: 78 · 2022: 114 · 2021: 135 · 2020: 110 · 2019: 150 · 2018: 127 · 2017: 132 · 2016: 152 · 2015: 166 · 2014: 182 · 2013: 200 · 2012: 207
- FWCI
- 55.92
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Endocrinology (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Endocrinology › Estrogen and related hormone effects
- Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Effects and risks of endocrine disrupting chemicals
- Health Sciences › Nursing › Nutrition and Dietetics › Phytoestrogen effects and research
- Keywords
- estrogen receptor beta, estrogen receptor alpha, phytoestrogens, xenoestrogens, estrogenic activity, ligand binding affinity, competitive binding, transcriptional activation, polychlorinated biphenyls, DDT, alkylphenols, bisphenol A, methoxychlor, chlordecone, coumestrol, genistein, zearalenone, kaempferol, apigenin, naringenin, quercetin, ipriflavone, biochanin A, daidzein, phloretin
- MeSH terms
- Binding, Competitive, Coumestrol, DDT, Environmental Pollutants, Estradiol, Estrogens, Estrogens, Non-Steroidal, Flavonoids, Humans, Isoflavones, Polychlorinated Biphenyls, Receptors, Estrogen, Structure-Activity Relationship, Transcription, Genetic, Zearalenone, Plant Preparations, Phytoestrogens
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